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Unusual formation of a thiacyclopent-2-ene by the reaction of 4,4′-dimethoxythiobenzophenone with tetracyanoethylene

✍ Scribed by Kentaro Okuma; Yoshikazu Tsujimoto

Book ID: 102227942
Publisher: John Wiley and Sons
Year: 2001
Tongue: English
Weight: 84 KB
Volume: 12
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.1041

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✦ Synopsis

Abstract

The reaction of 4,4′‐dimethoxythiobenzophenone (1a) with tetracyanoethylene (TCNE) afforded an unusual type of 2:1 adduct with the structure of thiacyclopent‐2‐ene (5a). On the other hand, the reaction of thiobenzophenone (1b) with TCNE afforded the corresponding thiophene, the normal 2:1 adduct (2b). The mechanism of the formation of 5a is discussed. © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:259–262, 2001

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